Ethyl Acetate → 5-Bromo-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine

HRID 928588

Reaktionsgleichung

[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.[N:12]1([CH2:17][CH2:18][O:19][CH2:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C.O>[Br:1][C:2]1[C:10]2[C:9]([N:24]3[CH2:25][CH2:26][CH:21]([CH2:20][O:19][CH2:18][CH2:17][N:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)[CH2:22][CH2:23]3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

5-Bromo-4-chlorothieno[2,3-d]pyrimidine (828 mg 3.33 mmol) in dry acetonitrile (13 mL) was treated with 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine (1.057 g, 5.0 mmol,) and potassium carbonate (687 mg, 5.0 mmol) and heated at 110° C. for 30 min in a microwave. The reaction was then poured into ethyl acetate (50 mL) and water (30 mL) and the ethyl acetate layer separated, dried over sodium sulphate and concentrated in vacuum to give 5-bromo-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine (1.322 g, 3.11 mmol, 93%). LCMS RT=2.91 min. M+1=427.

Aufarbeitung

customthe ethyl acetate layer separated
dry with materialdried over sodium sulphate
concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag: ord-a26ce6502f2e45e6aea926548a44d7cb
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09290511B2

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